2-Decarboxy-2-aminomethyl-19,20-didehydro-13,14-dihydro-PG1 compounds

ABSTRACT

The present invention provides novel 2-decarboxy-2-aminomethyl-19,20-didehydro-13,14-dihydro-PG 1  compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.

CROSS REFERENCE TO RELATED APPLICATIONS

The present application is a division of Ser. No. 026,066, filed Apr. 2, 1979, pending issuance as a United States Patent.

BACKGROUND OF THE INVENTION

The present invention relates to novel prostaglandin analogs. Particularly, these compounds are analogs of the prostaglandins wherein the C-20 - C-19 position is unsaturated, i.e., 19,20-didehydro-PG compounds. Most particularly, the present invention relates to novel 2-decarboxy-2-aminomethyl-19,20-didehydro-13,14-dihydro-PG₁ compounds, a disclosure of the preparation and use of which is incorporated here by reference from U.S. Pat. No. 4,228,104, filed Apr. 2, 1979.

PRIOR ART

Prostaglandin analogs exhibiting unsaturation in the C-17, C-18, or C-20 position are known in the art. See, for example, U.S. Pat. No. 3,919,285, German Offenlegungsschrift No. 2,635,985 (and its corresponding Derwent Farmdoc CPI No. 10302A), and U.S. Pat. No. 4,064,351 for examples of such compounds. See also the references cited in United States Ser. No. 026,066.

SUMMARY OF THE INVENTION

The present invention particularly provides:

A compound of the formula ##STR1## wherein D is (1) --(CH₂)₃ --(CH₂)_(g) --CH₂ --,

(2) --(CH₂)₃ --CF₂ --,

(3) --(CH₂)₃ --O--CH₂ --,

(4) --(CH₂)₂ --O--(CH₂)₂ --,

(5) --CH₂ --O--(CH₂)₃ --, ##STR2## wherein g is zero, one, two, or three; wherein Q is ##STR3## wherein R₅ is hydrogen or methyl, wherein R₇ and R₈ are hydrogen, alkyl of one to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different, wherein R₂ is hydrogen, hydroxyl, or hydroxymethyl; wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro; wherein W is ##STR4## and wherein X is --CH₂ CH₂ --.

The compounds of the present invention are particularly useful for inducing prostaglandin-like biological effects, as is described in United States Ser. No. 026,066. Uses of compounds in accordance with the present invention include, therefore, anti-asthmatic indication. 

I claim:
 1. A compound of the formula ##STR5## wherein D is (1) --(CH₂)₃ --(CH₂)_(g) --CH₂ --,(2) --CH₂)₃ --CH₂ --CF₂ --, (3) --(CH₂)₃ --O--CH₂ --, (4) --(CH₂)₂ --O--(CH₂)₂ --, (5) --CH₂ --O--(CH₂)₃ --, ##STR6## wherein g is zero, one, two, or three; wherein Q is ##STR7## wherein R₅ is hydrogen or methyl, wherein R₇ and R₈ are hydrogen, alkyl of one to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different, wherein R₂ is hydrogen, hydroxyl, or hydroxymethyl; wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro; wherein W is ##STR8## and wherein X is --CH₂ CH₂ --. 